4-Chloroaniline → HCID 24958478, compound

Participants

Reaction Steps

2-(Quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid (80 mg, 0.251 mmol) was suspended in N,N-dimethylformamide (1.2 mL) then added 4-chloroaniline (45 mg, 0.351 mmol), 1-hydroxy-7-azabenzotriazole (34 mg, 0.251 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (72 mg, 0.376 mmol) and N,N-diisopropylethylamine (89 mg, 0.878 mmol). The reaction mixture was stirred at room temperature for two days then concentrated under vacuum. The crude material was purified by silica gel chromatography (50% to 67% ethyl acetate/hexane) to afford N-(4-chlorophenyl)-2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide (92 mg) as a white solid. MS (ESI, pos. ion) m/z: 428.1 (M+1).

Provenance & Evidence